Reaktion #487564

Reaktionsgleichung

2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione

2-methyl-4-chloro-phenylboronic acid

cesium fluoride

→

2-(4′-chloro-4-ethyl-2′-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe warm reaction mixture
2. 2
   Filtrationis filtered
3. 3
   Waschenwashing the filter cake with 9:1 dichloromethane
4. 4
   EinengenThe mixture is concentrated under reduced pressure
5. 5
   Sonstigethe residue is purified by column chromatography on silica gel

Vorschrift

A mixture of 2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione (0.194 g, 0.6 mmol), 2-methyl-4-chloro-phenylboronic acid (0.153 g, 0.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane 1:1) (80 mg, 0.098 mmol) and cesium fluoride (0.608 g, 4 mmol) are stirred together in 1,2-dimethoxyethane (4 ml) and the reaction mixture is heated at 80° C. overnight. The warm reaction mixture is filtered, washing the filter cake with 9:1 dichloromethane:methanol. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethyl-2′-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione.

Quelle